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United States Patent 19 11 Patent Number: 5,728,376 Attygalle Et Al

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United States Patent 19 11 Patent Number: 5,728,376 Attygalle Et Al IIIUSOO5728376A United States Patent 19 11 Patent Number: 5,728,376 Attygalle et al. 45) Date of Patent: Mar. 17, 1998 54. TETRADECATRIENYLAND Attygalle, et al. "Gas-Phase Infrared Spectroscopy for TETRADECADENYLACETATES AND Determination of Double Bond Configuation of Monoun THER USE ASSEX ATTRACTANTS FOR saturated Compounds." Analytical Chemistry, TOMATO PESTS 66(10): 1696-1703 (1994). Nesbitt. et al., "Identification of components of the female 75) Inventors: Athula B. Attygalle, Ithaca, N.Y.; sex pheromone of the potato tuber moth, Scrobipalipopsis Gulab N. Jham, Vigosa, Brazil; solanivora, ' Entomol. exp. appl. 38:81-85(1985). Alessvatoš, Prague, Czech Rep.; Rosa Persoons, et al. "Sex pheromone of the potato tuberworm T.S. Frighetto, Campinas, Brazil moth, Phthorimaea operculella: isolation, identification and field evaluation." Ent. exp. & appl. 20:289-300 (1976). 73) Assignee: Cornell Research Foundation, Inc., Renou, et al., "L'acétoxy-1 dodécéne 3E, composant prin Ithaca, N.Y. cipal de la phéromone sexuelle de la betterave: Scrobipalpa ocellatella Boyd. (Lépidoptere Gelechiidae).” Z. ang. Ent. (21) Appl. No.: 428,406 90:275-279 (1980). Roelofs, et al. "Lepidopterous sex attractants discovered by 22 Filed: Apr. 25, 1995 field screening tests”. J. Econ. Entomol. 63(5):969-974 (51) Int. Cl' ......................... A01N 31/02; CO7C 33/02: (1970). CO7C 33/048; CO7C 21/02 Svatos, et al., "Synthesis of deuterium labeled polyunsatu (52) U.S. Cl. .......................... 424/84; 560/261; 568/849; rated fatty acids." Tetrahedron Letters. 35(51):9497–9500 568/850; 568/873; 568/903; 43/132.1 (1994). 58 Field of Search ..................... 424/405, 84; 560/261; Primary Examiner-Edward J. Webman 568/849, 850, 873,903 Attorney, Agent, or Firm-Nixon, Hargrave, Devans & Doyle 56 References Cited ABSTRACT U.S. PATENT DOCUMENTS 57 3,980,771 9/1976 Meijer et al. ............................. 424/84 The present invention is directed to compounds useful as 3,991,125 11/1976 Labovitz et al. ... 424/84 moth attractants and to methods for controlling populations 4,147,771 4/1979 Struble et al. ............................ 424/84 of the tomato moth Scrobipalpuloides absoluta with these 4,189.614 2/1980 Samain ............ ... 568/908 compounds. The compounds are 3,8,11-tetradecatrienyl 4,284,622 8/1981 Underhill et al. ........................ 424/84 acetates, 3.8-tetradecadienyl acetates, 3, 11-tetradecadienyl 4,296,042 10/1981 Muchowski et al. 260/345.9 R acetates, and 8.11-tetradecadienyl acetates. Preferred com 4,609.498 9/1986 Banasiak et al. 260/410.9 R pounds are (3E,8Z.11Z)-3,8,11-tetradecatrienyl acetate, (3E, 4,654,461 3/1987 Drake et al. ... 585/600 8Z)-3,8-tetradecadienyl acetate, (3E, 11Z)-3, 11- tetradecadi 4,834,745 5/1989 Ogawa et al. ... ... 424/409 enyl acetate, and (82.11Z)-8-11-tetradecadienyl acetate. The 4,844,916 7/1989 Ogawa et al. ....... ... 424/409 compounds can be used as an attractant in moth traps 5,236,715 8/1993 McDonough et al. ................... 424/84 5,252,326 10/1993 Novotny et al. ......... ... 424/54 comprising, in addition to the compounds, a moth restraint. 5,380,524 1/1995 McDonough et al..................... 424/84 Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as OTHER PUBLICATIONS a moth control composition. Synthesis of (3E.8Z.11Z)-3.8. Attygalle, "Gas phase infrared spectroscopy in characteriza 11-tetradecatrienyl acetate is described. tion of unsaturated natural products.” Pure & Appl. Chem. 66(10/11):2323-2326 (1994). 62 Claims, 5 Drawing Sheets OO/ PEAK 2 PEAK --- 22:O2 23:22 24.2 26:02 27:22 U.S. Patent Mar 17, 1998 Sheet 1 of 5 5,728,376 o CN - U O O na n N N Na O CO O VO N 92 w N O s N 2 d ) s in S n S. N n O 9 C O N n r N O VO O ar S On 9 N 3SNOS3& 30 NWONSW U.S. Patent Mar. 17, 1998 Sheet 2 of 5 5,728,376 woul.......as a cowr-erarwira-Re Frymaverseasureseries assovernow co-open-wxor O a is s sa o 4. s a 4 is a g 8 ww.exex mayorr 8 g S g 9 g O O. O. O O. O. O. O O. O. S On Oo N to ur N r ra. ONONOSB& S3WWO 99W. N3O3 U.S. Patent Mar. 17, 1998 Sheet 3 of 5 5,728,376 4-1-12N \SN 30cm &z/ I v--A \ \S2. H |N INNINr. CONTROL 1 g 10 ug 100g FEMALE F.G. 6 U.S. Patent Mar. 17, 1998 Sheet 5 of 5 5,728,376 HNHHNTH | | | |N| || | | |N|NNN 3-LAM L.-5AM 5-6AM 6-7AM 7-8AM 8-9AM FIG.7 5,728,376 1 2 TETRADECATRENYLAND In recent years, compounds known as pheromones have been recognized as useful components of successful pest TETRADECADENYLACETATES AND control programs. A pheromone is generally defined as a THEIR USE ASSEXATTRACTANTS FOR chemical substance secreted by living organisms, including TOMATO PESTS insects, to convey information or produce a specific response in other individuals of the same species. Sex This invention was made through the support of the pheromones may be a single compound but typically take National Science Foundation (Grant INT9202380). The the form of a complex, volatile blend of compounds which Federal Government may retain certain rights in the inven is, for example, secreted during the mating cycle. As such, tion. sex pheromones often serve as "attractants"; that is, the FIELD OF THE INVENTION pheromone attracts insects of the same species to the loca This invention relates to moth attractants and to methods tion of the pheromone emission. Attractants for many species of moth have been identified. for synthesizing and using these attractants. For example, Persoons et al. "Sex pheromone of the potato BACKGROUND OF THE INVENTION 15 tuberworm moth, Phthorinaea operculella: isolation, iden Tomato (Lycopersicon esculentum) is an economically tification and field evaluation." Entomol. Exp. Appl. important plant which is cultivated extensively all over the 20:289-300 (1976), disclose the use of (4E,7Z.10Z)-4,7,10 world. However, tomato is extremely susceptible to insect tridecatrienylacetate, together with the corresponding diene, attack by Scrobipalpuloides absoluta (Lepidoptera: (4E.7Z)-4,7-tridecatrienyl acetate, as a sex attractant for Gelechiide) (Gallo et al. in Manual de Entomologica 20 Phthorimaea operculella. Nesbitt et al., "Identification of Agricola, 2nd ed., Ceres, ed., Sao Paulo, Brazil, 649 (1988)). components of the female sex pheromone of the potato tuber In the past, the pest has been known as Scrobipalpa absoluta moth, Scrobipalipopsis solanivora,' Entomol. Exp. Appl., and Scrobipalpulpa absoluta (Meyrick). It is known locally 38:81-85 (1985), have identified (E)-3-decen-1-yl acetate as as "traga-do-tomateiro” in Brazil and as "polilla del tomate" a pheromone constituent of the potato tuber moth. Scrobi in other Latin American countries. The pest is particularly 25 palposis solanivera Povolny. Pheromones for some insects active in Latin America where it causes severe damage in all from the Scrobipalpa family have also been identified. These tomato growing countries including Venezuela, Columbia, include: (E)-3-tridecen-1-yl acetate for the tobacco stem Chile, Ecuador, Bolivia, Peru and Uruguay. Brazil, which borer moth, Scrobipalpa heliopa (Lower) (Baker et al. "Sex has about 55,000 acres under tomato cultivation, has been pheromone of tobacco stem borer Scrobipalpa heliopa particularly affected. Since 1981, when Moreira et al., (Lower) (Lepidoptera: Gelechiidae)." J. Chem Ecol., "Ocorrencia de Scrobipalpula absoluta danificando 11:989–998 (1985)) and (E)-3-dodecen-1-yl acetate for the tomateiro rasteiro em Jaboticabal," S.D. in Congresso sugar beet moth, Scrobipalpa ocellatella Boyd (Renou et al. Brasileiro de Entomologic Fortaleza Ce, 58 (1981), first "L'acétoxy-1 dodécene 3E, composant principal de la reported the pest in Brazil in the state of Sao Paulo. phéromone sexuelle de lateigne de la betterave: Scrobipalpa infestation has spread to other states, such as Minas Gerais, 35 ocellatella Boyd. (Lépidoptère Gelechiidae)," Z. ang. Salvador, Espirito Santo and Rio de Janeiro. Losses of up to Entomol, 90:275-289 (1980)). 100% have been described. No attractant has yet been identified for the tomato moth, The need to suppress Scrobipalpuloides absoluta popu Scrobipalpuloides absoluta, and, therefore, blanket spraying lations ("S. absoluta") has resulted in the application of large of broad-based insecticides, with all its associated limita amounts of conventional, broad-based insecticides by blan tions and adverse impacts, remains the dominant control ket spraying. The method, however, has serious limitations. method. For these and other reasons, a need exists for It is now well established that continuous or repeated pheromone attractants for S. absoluta and methods of pesticide use results in the emergence of insect strains which employing this attractant to control S. absoluta populations. resist the chemicals being applied, making subsequent insect SUMMARY OF INVENTION control more difficult. Furthermore, application of broad 45 based pesticides upsets delicate natural balances by elimi The present invention relates to attractants for moths as nating non-targeted species, including natural predators of well as to the synthesis and use of these compounds. One the pest and pollinators. The use of insecticides also aspect of the present invention relates to an isolated 3,8,11 adversely impacts the farmers, both economically and medi tetradecatrienyl acetate. cally. The cost of broad-based insecticides and the cost of 50 Another aspect of the present invention relates to an their application place a heavy financial burden on poor isolated tetradecadienyl acetate. The tetradecadienyl acetate farmers. The use of pesticides also subjects farmers and is selected from the group consisting of a 3.8- other inhabitants living near tomato fields to the hazards of tetradecadienyl acetate, a 3.11-tetradecadienyl acetate, and exposure.
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